Location: Windermere
Keyword(s): Olympia High
Keyword(s) High School: Olympia High
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5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$25,000Listed 06/19/2026 6:45PM MLS ID: O6418570
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6424 Built: 1992Community: IsleworthSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Windermere Elem
High School: Olympia High
Tax Year:
Middle School: Chain of Lakes Middle
Remarks: Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living. Also available for sale.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$15,00076 Days on yellowkey MLS ID: O6396406
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Community: LakesSpa: YesSingle Family
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Lease or Lease Purchase available! Experience true lakefront living on the famed Butler Chain of Lakes in this exceptional custom home offering 137 feet of pristine shoreline on nearly one acre of high, dry land. Enjoy sweeping panoramic water views, refreshing lake breezes, and even nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and enter through an impressive solid cedar door with artisan leaded glass. Inside, the great room features soaring 23’ cathedral ceilings and a dramatic Tennessee river rock fireplace. The showstopping formal dining room is wrapped in oversized picture windows that perfectly frame the lake. Designed for comfort and convenience, the majority of the living space including all bedrooms is on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a bright breakfast area with incredible water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-style bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Secondary bedrooms are generously sized with ample closet space and well-appointed baths, including a steam shower. Outdoor living is unmatched with mature landscaping and colorful gardens, plus a motorized screened lanai with a summer kitchen featuring a pizza oven, prep area, grill, refrigerator, and TV. Relax by the pool, heated spa, and gas firepit, all positioned to take advantage of the desirable southern exposure for comfortable outdoor enjoyment. Boaters will love the rare, partially enclosed grandfathered-in dock with boat lift and side jet-ski lift. Additional features include newer doors and windows, a tile roof, and a custom floor plan maximizing lake views throughout. The Lakes community also offers a boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes to major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
9701 LAKE ISLEWORTH CT, WINDERMERE, FL 34786
$12,500115 Days on yellowkey MLS ID: O6385693
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3535 Built: 2000Community: IsleworthSingle Family
Remarks: RECENTLY RENOVATED within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a gas fireplace. Enjoy the outside grill area and large fenced-in yard. The home has an oversize 2 car garage with a golf cart entrance for those golf enthusiasts.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
820 EAST BLVD, WINDERMERE, FL 34786
$6,00017 Days on yellowkey MLS ID: O6407655
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1713 Built: 1952Community: Windermere TownSingle Family
Remarks: Fully Furnished Executive Rental in downtown Windermere! Welcome to Sunrise on the Lake, a beautifully renovated, fully furnished executive home on Lake Bessie in Windermere. Tucked along winding lakeside roads, this peaceful retreat is perfectly positioned for stunning sunrises, refreshing lake breezes, and panoramic water views. From the moment you arrive, you will appreciate the exceptional curb appeal and expansive front deck overlooking the lake. Chicago brick pavers lead to a mostly single-level, open-concept layout designed for comfort and entertaining. The European inspired living space features a bright dining area with large picture windows and a welcoming family room with premium amenities, including a Sony flat-screen TV, Bose soundbar, electric fireplace, stand-up arcade with 100+ games, foosball table, plus board games and books. The fully equipped kitchen offers stainless steel appliances, remarkable lake views, and opens to the dining area with comfortable seating for eight. Bedrooms provide relaxing, private spaces with views of the home’s half-acre setting. Outside, enjoy a private moon garden with orchids, a shaded dining area beneath a grand oak tree, and a spacious deck perfect for soaking up the Florida sun and enjoying the calm water. The home has recently undergone a complete remodel, with new or newer furnishings throughout, including updated appliances.
1243 DINGENS AVE, WINDERMERE, FL 34786
$3,000431 Days on yellowkey MLS ID: O6300024
REDUCED by $1,000 (25.0%) on 05/02/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1928 Built: 1969Community: Gotha TownSingle Family
Remarks: WONDERFUL WELCOME HOME IN WINDERMERE. READY TO MOVE IN. TOP RATED SCHOOLS IN A FAMILY COMMUNITY, NEAR DISNEY, DINING AND ENTERTAINMENT, MAY BE RENTED FULL FURNISHED, FEELS LIKE COUNTRY LIVING, BUT CLOSE TO EVERYTHING, so bring your boat, camper, or build the Gotha Park is just a short walk away, offering tennis courts, a pavilion, and a tot lot for the little ones. LOCATION, LOCATION, LOCATION! Zoned for Thornebrooke Elementary, a top-rated school. Hungry but don’t feel like cooking? Take a leisurely stroll to Yellow Dog Eats—your four-legged friend will love the walk, too! At the end of the day, this isn’t just a house—it’s your own personal retreat. Whether you’re relaxing, entertaining, or making memories, this is where everyone will want to gather. Listing rent monthly front house 3 bedroom and 2 bathroom living area, dinning area, Family room. Also the in law in the backyard one bedroom or loft with kitchenette and living area just for $1K add to the lease. Schedule your private tour today!
Listing is courtesy of: REALMULTIPROPERTY LLC (407-412-8598)
Listing Agent: Peter Useche (407-412-8598)
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